50 prompts for solo owners

Act as an assistant to a solo business owner. Search my inbox for every unread email from [the last 24 hours / since Friday / this week] and read the sender, subject line and first two lines of each.

Sort them into four groups: NEEDS ME (a real decision or my expertise), QUICK REPLY (I can answer in one line — draft that line), WAITING ON THEM (no action from me, just track it), and IGNORE (newsletters, notifications, noise).

For anything with money or a deadline attached, flag it and say what the deadline is. Do not write long explanations — I want to scan this in thirty seconds.

Read only. Do not reply, archive, label, delete or send anything — I will decide what happens next.

Here are three emails I have written in the past. Study how I write: sentence length, how formal I am, whether I use contractions, how I open and close, and what I never say.

[paste three of your own emails]

Now draft a reply to the email below, matching that voice exactly. Do not add pleasantries I would not use. Keep it the same length I would have written. Give me the draft only, no commentary.

Email to reply to:
[paste the email]

I need to decline this piece of work. The real reason is [not enough time / the budget is too low / it is outside what I do / I do not want to work with them].

Write a short reply that declines clearly — no maybe, no leaving the door ajar by accident — but stays warm. If there is an honest alternative I can offer (a later date, a smaller scope, a referral), include one. Do not apologise more than once, and do not over-explain: one sentence of reason is enough.

Their message:
[paste the enquiry]

Below is a long, unstructured email from a customer describing what they want.

Extract: (1) what they are actually asking for, in one sentence; (2) the specific deliverables; (3) any dates or deadlines mentioned, including vague ones like "before the summer"; (4) anything about budget; (5) the questions I still need answered before I can quote — these matter most, so be thorough and list the gaps they did not realise they left.

Email:
[paste it]

A client went quiet after [describe the last exchange — I sent a quote / they asked for changes / we agreed next steps]. It has been [number] days.

Write a short follow-up. Rules: no guilt ("just circling back", "I know you're busy"), no apology for following up, and give them an easy way to answer — ideally a question they can reply to with one word or a yes/no. Under 80 words.

Last message in the thread:
[paste it]

I get asked this same question constantly: [paste the question].

Write a reply I can reuse. It should answer the question completely so there is no obvious follow-up, be friendly but brief, and end by pointing them to the next step if they want to go ahead.

Then give me two variants: a warm one for existing customers, and a slightly more formal one for cold enquiries. Mark clearly where I would need to personalise each one.

A customer is unhappy. Here is their message and here is what actually happened from my side.

Their message: [paste it]
What actually happened: [your version]
What I am willing to offer: [refund / redo / discount / nothing, just an explanation]

Write a reply that acknowledges the specific thing that went wrong (not a generic "sorry you feel that way"), states plainly what I will do, and does not admit fault for things that were not my fault. Calm, short, no defensiveness. If their message contains an unreasonable demand, address it directly rather than ignoring it.

I am going to miss a deadline. Details:

Original deadline: [date]
Realistic new date: [date]
Why: [honest reason]
What is already done: [progress]

Write the email. Lead with the new date rather than burying it after the excuses, keep the reason to one sentence, and show what is already finished so they can see it is progressing rather than stalled. Offer something concrete that reduces the impact on them if there is one.

Below is an email thread with [number] messages. Summarise it as:

DECIDED — what was actually agreed, with who agreed it.
OPEN — questions raised but never answered.
MY ACTIONS — what I committed to, with any dates.
THEIR ACTIONS — what they committed to.

Quote the exact wording for anything involving money or dates. If two messages contradict each other, say so rather than picking one.

Thread:
[paste it]

Write an out-of-office reply for [dates]. I run a [type of business] on my own.

It should: say when I am back, tell people what to do if it is genuinely urgent (define urgent so people do not all self-select), and tell everyone else what to expect. If there is a self-serve answer for the most common enquiry — [describe it] — point them there so those emails never need my reply at all.

Under 100 words. Do not sound like a corporate auto-responder.

Write a first reminder for an overdue invoice.

Invoice: [number] for [amount], due [date], now [number] days late.
Client: [name], relationship is [new / long-standing / a bit strained].
What the work was: [description]

Tone: assume it was simply missed, because it usually was. No passive aggression, no "as per my previous email". Restate the amount, the invoice number and how to pay in a single scannable line, and ask one direct question that makes it easy to reply. Under 90 words.

Write a three-message sequence for chasing an unpaid invoice, to be sent at day 7, day 21 and day 35 past the due date.

Invoice: [amount], for [work], client [name].
My payment terms: [terms]
Late fee, if any: [details or "none"]

Message 1: assume oversight, friendly.
Message 2: firmer, restate the terms, ask for a payment date specifically rather than just payment.
Message 3: final notice before [next step]. Professional, unemotional, clear about what happens next and by when. No threats, no anger — just consequences stated plainly.

Keep every message under 120 words.

I want to start asking for a [percentage]% deposit before I begin work. I do [type of work] for [type of customer].

Write: (1) the two or three sentences I put in my quote explaining the deposit; (2) a short reply for when someone pushes back and asks to pay on completion.

Frame it as how the business works and what it secures for them — their slot in the diary, materials ordered — rather than as protection against them personally. Confident, not apologetic.

I am raising my prices from [old] to [new], effective [date]. I have not raised them since [date]. Reason: [costs / demand / undercharging].

Write the message to existing clients. Rules: state the new price and the date in the first three lines — do not bury it. Give one honest sentence of reason and stop; over-justifying invites negotiation. Say what, if anything, stays the same for work already booked. Do not apologise for the increase.

Then write a short reply for anyone who asks me to keep the old rate.

Below is how a customer described what they want. My rates are [hourly rate / day rate / typical project pricing].

Turn it into a quote with: scope in plain language, itemised deliverables, price, timeline, and — most importantly — an ASSUMPTIONS section listing everything I have had to guess. Anything not in scope goes in an explicit EXCLUDED list, because that is where scope creep starts.

Flag anything in their description that is too vague to price safely.

Their description:
[paste it]

Rewrite my payment terms so a normal person understands them at a glance.

Current terms: [paste, or describe: deposit, when the balance is due, what happens if late, accepted payment methods, cancellation]

Use short sentences and no legal-sounding phrasing where a plain word will do. Keep every obligation intact — do not soften a term into something unenforceable. Output as a short bulleted list I can paste at the bottom of a quote.

Note: I will have a professional check anything legally binding before I use it.

A client keeps adding to a project that we already agreed and priced.

Agreed scope: [what was agreed]
What they are now asking for: [the extras]
What that adds: [time and cost]

Write a reply that: says yes to doing the work, prices it as an addition, and shows the difference between what we agreed and what is being asked without making them feel caught out. Give them a clear choice — add it at this cost, or keep the original scope. No resentment in the tone. Then give me one sentence I can put in future quotes to prevent this.

Here is my list of invoices with amounts, dates sent, due dates and paid/unpaid status.

Give me a five-line summary: total owed to me right now; the amount overdue and by how long; who to chase first and why; how much came in this [week/month] against the same period before; and anything that looks wrong — a missing invoice, a duplicate, a client whose payments are slowing down.

Be blunt about the client whose behaviour is getting worse, even if the total still looks fine.

Data:
[paste your invoice list]

I am owed [amount] by a large company. My contact there is [name/role], but the payment is stuck somewhere in their process.

Write two messages: one to my contact asking them to unblock it internally — making it easy for them to forward — and one to their accounts payable inbox that includes every reference a payments system needs: invoice number, PO number [if any], amount, date, and my bank details.

Assume nobody is being malicious and everybody is busy. Short, factual, easy to act on.

Help me decide whether to take this job.

The work: [description]
Their budget: [amount]
My realistic estimate: [hours], and I usually underestimate by about [percentage]%
My target rate: [amount per hour]
What else I would turn down to do it: [other work, or nothing]

Calculate the effective hourly rate including the admin, travel and revisions I have not counted. Then tell me plainly: take it, negotiate it, or walk. If negotiate, give me the number to ask for and one sentence to ask with.

Someone has enquired about [service]. Write a reply that gets them booked in one exchange rather than five.

Include: a one-line confirmation that I can help, three specific slots with dates and times, how long it will take, what it costs [or how pricing works], and what they need to do or have ready.

Offer exactly three slots — more creates dithering. End with a single question that only needs a one-word answer.

Their enquiry:
[paste it]

Write appointment reminders for [type of appointment], to go out [when — e.g. 48 hours and 2 hours before].

Each one should include the date, time, place [or link], and what they should bring or prepare. Add one line on what happens if they cannot make it — with the reschedule route made easy, because a person who can rebook in one tap does not simply vanish.

Keep the 48-hour one under 60 words and the 2-hour one under 25. Write them for SMS as well as email.

Someone missed their appointment on [date] and did not get in touch.

Write a short message that assumes something came up rather than that they could not be bothered, offers two new slots, and mentions my cancellation policy [describe it] only if I actually intend to apply it. No guilt trip — the goal is a rebooking, not an apology from them.

Under 60 words.

Write my cancellation policy. The rules: [e.g. 24 hours' notice, deposit non-refundable after X, late arrivals lose their slot].

Write it in friendly, plain language that still leaves no wiggle room about the deadline or the amount. Explain briefly why it exists — a slot held is a slot nobody else could book — because people follow rules they understand.

Give me two versions: a short one for the booking confirmation, and a fuller one for my website.

I need to move an appointment I had already confirmed.

Original: [date and time]
Reason: [honest reason]
Alternatives I can offer: [slots]

Write the message. Apologise once, properly, and then move straight to fixing it. Give specific alternatives rather than "when suits you?" — that pushes the work back onto them. If the inconvenience is significant, suggest one thing I could offer to make up for it.

I do [type of appointment], usually [length]. Too much of the start gets spent on things I could have known in advance.

Write the intake questions I should ask when someone books. Maximum eight. Every question must change what I actually do or bring — cut anything that is merely nice to know. Use plain wording a customer will understand, mark which are required, and put the one that most often causes a wasted appointment first.

Write a follow-up to send [timing] after a [type of appointment].

It should: thank them briefly, give any aftercare or next-steps they need, ask for a review with a direct link, and mention rebooking if that is relevant for this kind of work.

Put the useful content first and the asks last. Keep the review ask to one sentence with a specific question they can answer, since "leave us a review" gets ignored and "what did you think of X?" gets a paragraph.

I am booked up until [date]. Write the reply for new enquiries.

It should not sound like a rejection. Say when I next have space, offer to put them on a waitlist with a clear explanation of how the waitlist actually works, and give them one useful thing in the meantime [a tip, a resource, a referral].

Being busy is proof of quality — let that show without boasting about it.

Below are my rough notes from a phone call.

Turn them into: a customer-facing confirmation of what we agreed, a calendar entry title and description, and a private checklist of what I need to prepare or bring.

Flag anything in my notes that is ambiguous — if I wrote a time without a date, or a price without saying whether tax is included, ask me rather than guessing.

Notes:
[paste them]

Here are my appointments for next week with times, locations and types.

Rearrange them to cut travel and context-switching: group jobs in the same area on the same day, cluster similar types of work together, and protect at least one uninterrupted block for [admin / deep work].

Show the before and after with the time saved. List which customers I would need to ask to move, ordered by who is most likely to say yes.

Appointments:
[paste them]

Below are five things I have written — posts, emails, anything in my own words.

Analyse them and produce a VOICE PROFILE covering: typical sentence length and rhythm, vocabulary I favour and words I never use, how formal I am, whether I use humour and what kind, how I open and close, and the three things that most make my writing recognisably mine.

Then write two sample paragraphs on [topic] using that profile.

Save the profile — I will paste it at the top of future prompts.

My writing:
[paste five samples]

—This one starts with a voice profile. Make it first with Teach the AI how you write, then paste it in.

My voice profile: [paste it]
My customers: [who they are and what they worry about]
The idea: [one sentence]

Turn that single idea into five posts for [platform], one per weekday. Each must take a genuinely different angle — the story, the practical how-to, the common mistake, the myth worth correcting, the customer question answered — so that someone who sees all five does not feel talked at twice.

No hashtag soup, no "let that sink in", no emoji unless my voice profile uses them.

—This one starts with a voice profile. Make it first with Teach the AI how you write, then paste it in.

A customer asked me this: [paste the question].

Write a post answering it. Open with the question in the customer's own words, because other people are wondering the same thing and will recognise themselves. Answer it properly and completely — do not hold the useful part back as bait. End with a soft pointer to how I help, no hard sell.

My voice profile: [paste it]
Length: [number] words.

—This one starts with a voice profile. Make it first with Teach the AI how you write, then paste it in.

Here is what I worked on this week: [rough notes — jobs done, problems solved, things learned, anything that went wrong].

Turn it into a newsletter for my customers. Pick the ONE thing most useful to them and lead with it — do not give me a diary of everything. Include a specific detail or number that only someone who did the work would know. End with one clear action.

My voice profile: [paste it]
Also give me three subject lines: one plain, one curious, one that states the benefit.

Rewrite the text below so my customers understand it. They are [description] and they do not know my industry's vocabulary.

For every technical term, either replace it with the everyday word or explain it in the same sentence. Keep the meaning exactly — do not dumb down the substance, just the language. Where I have written what something IS, rewrite it as what it DOES for them.

Then list any terms you kept and why they had to stay.

Text:
[paste it]

Turn this job into a short case study.

The customer: [type, no names needed]
Their problem: [what was wrong]
What I did: [the work]
The result: [outcome, with numbers if you have them]
What they said: [any quote]

Structure it as: the situation, what was at stake, what I did and why, the result. Lead with the customer's problem, not with me. Keep it under 300 words. If the result has no number in it, tell me what I should have measured so next time it does.

—This one starts with a voice profile. Make it first with Teach the AI how you write, then paste it in.

Take the piece below and rewrite it for each channel, not merely trimmed to fit:

- A short post for [platform] — [length]
- An email version with a subject line
- A caption for an image post
- Three lines I could actually say out loud in a video

Each version should open differently, because the same first line reused everywhere reads as broadcasting rather than talking.

My voice profile: [paste it]
Original:
[paste it]

Write my business description for [Google Business Profile / directory / marketplace].

Business: [what you do]
Area: [where]
What makes me different: [honestly]
What customers search for: [the words they actually type]

Work those search terms in naturally — a description that reads like keyword stuffing loses the click even when it wins the ranking. Lead with what I do and who for. Give me a version at [character limit] and a shorter one at half that.

Write a message asking a happy customer for a testimonial.

The job: [what you did]
The relationship: [how well you know them]

Do not ask for "a review" — ask two or three specific questions whose answers will read as a testimonial: what the situation was before, what they were worried about beforehand, what changed afterwards. Make it clear it will take two minutes and offer to write a draft for them to correct, since that converts far better than a blank box.

Then give me the follow-up for a week later if they do not reply.

Here is a list of the jobs I have done recently and the questions customers asked me: [paste].

Find 20 content ideas in it. Prioritise the questions that came up more than once — repetition is proof of demand. For each idea give the angle in one line, who it is for, and which format suits it.

Mark the three that would most likely bring in an enquiry rather than merely getting likes, and say why.

Below is everything currently in my head, in no order.

Sort it into: DO THIS WEEK (with a suggested day), DELEGATE OR AUTOMATE (say which, and what it would take), SCHEDULE LATER (with a date), and DELETE (things that will not matter in a month — be ruthless here, and tell me why).

Within "do this week", order by consequence-of-not-doing rather than by urgency-as-it-feels. Flag anything that is blocking someone else, since those come first regardless.

My list:
[paste it]

I do this task repeatedly and it lives entirely in my head: [describe the task, roughly, in whatever order it comes out].

Turn it into a procedure: numbered steps, what is needed before starting, the decision points and what to do at each, and what "done" looks like.

Then tell me which steps could be automated and which genuinely need a person. Ask me about any step where my description is too vague for someone else to follow it.

Design my onboarding for a new [type of client].

What has to happen: [contract, deposit, intake form, kickoff, access to things, first milestone]
Timeline: [how long before work starts]

Give me the sequence with timing, who does what at each step, and the actual text of each message I send. Flag the step most likely to stall — usually the one where I am waiting on them — and give me the chaser for it.

Keep the client's total effort to under [number] minutes.

I am choosing between [tool A] and [tool B] for [purpose].

What matters to me: [must-haves]
Budget: [amount per month]
My situation: solo, [technical comfort level], already using [existing tools]

Compare them on what I said matters, not on feature lists. Cover what it costs to leave each one later — exports, lock-in, who owns the data. Then recommend one and say what would have to be true for the other to win instead.

If neither fits, say so.

Here are my recurring subscriptions with costs and what each is for: [paste].

For each: what it costs a year, whether anything else on the list already does the same job, and how essential it actually is.

Then give me: total annual spend, the three to cancel first with the reason, anything I appear to be paying for twice, and anything where a cheaper tier would clearly do. Flag anything I have not obviously used based on what I have told you.

Draft the terms for [situation — e.g. late payment, cancellation, revisions, ownership of work].

My business: [type]. My customers: [type]. What I need protected: [the risk].

Write it in plain English, cover the situation that actually goes wrong rather than every theoretical one, and keep it short enough that people read it. Explain what each clause does in a note underneath.

I will have a qualified professional review this before I use it — flag anything you think particularly needs their eye, and anything that varies by jurisdiction.

Here is a list of my business expenses with dates, amounts and descriptions: [paste].

Categorise them the way [my accountant / my tax return] expects. Flag: anything that looks personal rather than business, anything unusually large for its category, duplicates, and anything with a description too vague to defend if questioned.

Give me a total per category and the month-by-month trend. Tell me which category is growing fastest.

I will have these checked by a qualified accountant — this is for organising, not tax advice.

I have to have an awkward conversation with [client / supplier / subcontractor].

The situation: [what happened]
What I need to come out of it: [the outcome]
What I am worried they will say: [their likely position]
What I will not accept: [your limit]

Give me: my opening two sentences, the three points I must make, a response to each pushback I am likely to get, and the sentence I use if it goes nowhere and I need to end it.

Be direct. I do not want a script that avoids the actual issue.

Here is my income and expense data for [period]: [paste].

Tell me: what I earned and kept, my best and worst months and any pattern behind them, which type of work makes the most per hour, which customers make up what share of my income, and what my costs did over the period.

Then the uncomfortable bit: what is the biggest risk visible in this data — over-reliance on one customer, a shrinking margin, a service that is not worth doing? Say it plainly.

I am deciding whether to keep doing [task] myself or pay someone.

Time it takes me: [hours per month]
What I would earn doing paid work in that time: [amount per hour]
Cost to outsource: [amount]
How well I do it: [honestly]
How much I would still have to manage it: [estimate]

Work out the real cost of both options including the managing, the fixing, and the handover time. Then tell me which to do. If the answer is "automate it instead of hiring", say that and describe the flow.